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Jenna Peterson was in a quandary, and hoped she wouldn’t miss out on something she really wanted to do. For the last three weeks, she had been meeting her high school’s assistant dean of students, Brian Hanson, in his office, where they indulged in the best sex she had ever known. The first time had been when she was caught cheating on an exam and sent in to see him. By sucking him off, Jenna had avoided being expelled, besides giving both him and herself a really great time. Since then, they have done other wonderful things on the old couch in his office, and the young hotty is getting a better, and far more enjoyable education than she could possibly have expected.
She had to attend classes, of course, and Jenna knew he saw other students, sometimes actually counseling them, as well as performing other tasks, but they had been meeting whenever they could. Their next tryst was scheduled for two o’clock in the afternoon but that morning, which was a Friday, she woke up to find her menses had started a few days earlier than expected.
That wouldn’t dampen her ardor; she was even hornier than usual when she was in that condition, but Jenna was unsure of what Mr. Hanson would want to do. He almost certainly wouldn’t want to eat her pussy the way he usually did, but would he even be willing to fuck her under the rather messy circumstances? At a minimum, she could suck him off and swallow his cum while playing with her clit until she climaxed, but Jenna was horny enough that she would have much preferred the feel of a cock plunging in and out of her.
At two o’clock, minutes after changing her tampon, she stepped into his office and, after looking around and seeing nobody but him there, she entered the room and closed and locked the door behind herself. As he usually did, the assistant dean smiled at her and got up to meet her and steer her in the direction of the couch that stood against the wall. On previous days, great things had happened to her, and to him as well, on that old piece of furniture, but Jenna was afraid their meeting that day would not the same kind of frolicking.
“Hi, Jenna. I’ve been looking forward to our meeting all day.” As Brian spoke, he embraced the beautiful blonde, and they shared a long, deep kiss.
“I have too, Mr. Hanson, but I’ve got bad news. My period started this morning. I hope we can do something, but I don’t know what.” As they embraced, she had felt his stiff cock pressing against her through his pants, making her even more eager for some good, hot sex with him.
Brian knew what he wanted to do, and he hoped Jenna would want to do it too. Since their trysts began, he had been aware that there was a good chance that one of them would coincide with a day she was in her menses, and he had thought about what they would do if and when that happened. He was familiar with the concept: “If your front door is out of order, it’s no big problem. Just use the back door until it gets fixed.” He was also aware that a lot of women would be grossed out over the idea of being fucked in the ass, and he didn’t know what Jenna would think of the idea.
He did have a certain amount of distaste about the idea of fucking a pussy when the woman was in her period. Brian would have gone that far if nothing else was available, but he would have been much too squeamish to even consider eating her out during that time of the month. If she was unwilling to take his cock up her ass, he would settle for a blow job and let her get herself off with her fingers on her clit, which is what they did the first time they got together in his office. Wanting to be prepared for when the question arose, he had stashed a small bottle of Aqualube along with a supply of condoms in one of the locked drawers of his desk. Brian hoped to be able to put it to use that day.
“Well, Jenna, I know one thing we can do, but I’m not sure you’ll be willing to do it.” Have you ever tried anal sex?”
Although she was just 18 years old, Brian was aware the sexy blonde student standing in front of him had extensive sexual experience, but he didn’t know exactly what she had done and what she hadn’t. Jenna had told him he was the only person to eat her pussy, but he found it rather hard to believe that her boyfriends would have been so ignorant as to pass up such a delightful treat. At the same time, he also knew that many young men, such as most male students of high school age, were macho enough to consider such things unmanly. He regarded that as being their loss, especially with a girl as beautiful and sensuous as Jenna.
“Anal sex? You mean in my butt?”
“Yes. Have you ever tried it?”
“Isn’t that for gay men? I’ve heard of it, but I’ve always heard it was something that gay men like to do.” During their frequent whispered discussions in the girls’ locker room, most of her friends expressed revulsion at such a yucky idea, but Jenna had been more curious than repelled.
“Gay men do it, but so do some women. There are even some women illegal bahis who like anal more than almost anything else.”
“I’ve never done it.” That was true enough; she had never been fucked like that, but Jenna had slipped a soapy finger inside her ass a few times while in the shower. It had felt funny, and quite nice, but she knew Mr. Hanson’s cock was a lot longer and thicker than her finger. Even so, her interest was piqued. If she had to, she would settle for sucking off Mr. Hanson while playing with her clit, but what she really wanted was to feel his big, hard cock going in and out of her body, and she believed that in her ass would be better than not getting it anywhere.
“Do you want to try it? You know you’ve always had fun with what we’ve done here, and this shouldn’t be that much different.”
“If I don’t like it, and I ask you to stop, will you stop? If that happens, I’ll just suck you off like I did the first time.”
“Of course. I would never force you to do anything you didn’t like.”
“Okay. But what do you want me to do?”
“This isn’t all that big a change. I’d love to start the way we usually do.” As he said that, Brian took hold of Jenna’s jersey and pulled it out of the waistband of her skirt.
She raised her arms, and he pulled it off over her head, freeing her large, succulent breasts, because Jenna never wore a bra when she had a date with the horny assistant dean, and rarely at any other time. Brian cupped the luscious twins in his hands and started licking their nipples, switching back and forth between them. So far, there hadn’t been anything different from what they did during other sessions, except his tongue against her pink nubbins felt even more erotic than usual, because her menses were making Jenna even hornier than she otherwise would have been. It felt so good and she was so aroused that the horny blonde was already cooing with pleasure and starting to look forward to fucking in the new way.
“Let’s lie down like we usually do,” he continued while steering her to the couch.
Jenna removed her shoes and sox and lay on her back while Brian went to his desk for the bottle of lubricant, condoms and some paper towels he knew they would need. After setting them on the floor under the couch, he knelt beside her and resumed licking her nipples. They quickly became fully erect, and his tongue could already detect the many tiny ridges that made up their hardness. For several minutes, he continued worshipping the lovely globes, switching back and forth between them, until he opened his mouth and drew one inside. While his lips formed a seal, he sucked on the luscious flesh while his tongue teased the nipple and areola. Jenna’s body was already squirming under him, which was also the normal progression of their sexual escapades.
“Mmmmmm, I love that,” she murmured. “I love it when you suck and lick my boobies.”
Having his mouth so delightfully full, Brian didn’t say anything, but he did glance up at Jenna’s pretty face. It was a mask of carnal bliss already, with her eyes closed and her mouth twisted in a grimace of joy. He smiled too, but only inwardly, and switched his attentions back and forth between her succulent breasts. Her movements became even more pronounced, until she was writhing on the couch and thrusting her breasts up into the face of the assistant dean.
Usually, Brian gauged when Jenna was ready to have him go down lower and start eating her pussy by the volume of the juices she would have been producing. That day, they were being soaked up by her tampon, and he was unable to enjoy their delectable aroma. He had to depend on the movements of her body under his face and the sounds of pleasure she was making. From the way Jenna’s body was thrashing on the couch and how her cooing had evolved to blissful moans, she seemed to be ready for the new experience. He reached down and unbuttoned her skirt and, when Jenna saw what he was doing, she raised her ass from the couch so the garment could be pulled all the way off.
“Okay. If you think you’re ready, kneel on the floor and lean against the mattress. Just relax,” he continued with his instructions when she was in the position he wanted.
Brian inserted his thumbs into the waistband of Jenna’s skimpy panties and pulled them around her lovely ass and down her thighs. She raised one knee at a time so he could pull them all the way off around her feet and set them aside. They weren’t wet, and he missed the usual fragrance, but he knew the fun he would be having would more than make up for that lack. Of course, he expected Jenna to have as much fun and climax before he did. Except for the time when she sucked him off, he had always made a point of seeing to that.
Before starting, Brian spread Jenna’s ass cheeks and surveyed the delightful place where he would be putting his cock that day. He had caressed her ass and hips and thighs before, during foreplay or while he was eating her pussy, but had never taken illegal bahis siteleri a really good look at Jenna’s backside before. He regretted the omission, because her ass was truly a thing of beauty. Both hips flowed out and around from her sexily plump waist, and the succulent hemispheres of her buttocks, with the cute dimple at the top of the cleft between them, curved away from her smooth back, and out and around and under, where they all merged with her legs.
The skin of both her thighs and her ass was a milky white and, when she reached back to spread Jenna’s cheeks, her cute little rosebud winked at him. Brian almost always ate a woman’s pussy before fucking it, and he would have treated her ass the same way if she had just emerged from a shower. Under those circumstances, his tongue would have spent a long time caressing the smooth, white skin inside her cheeks and just as long on her delectable pink rosebud, but he was not willing to do either without a thorough washing.
After letting go of Jenna’s ass, Brian put on his condom, picked up the bottle of lubricant and twisted off the cap. He had asked his friend, George Boxlicker, for advice on the best brand to use, and George had recommended Aqualube, so that was what Brian had gotten to use that day. “Reach back and spread your ass cheeks for me,” he instructed Jenna and she eagerly complied.
She really loved all forms of sex and was very much looking forward to getting Mr. Hanson’s cock stuffed into a new part of her body. While she held the two delightful ovals apart, Jenna felt him reach between them and, using his fingers, spread the tight hole that was about to be fucked. It already felt delicious and wicked, and she quivered in anticipation. The next new experience was having something pressed against the tiny opening and twisted until it popped through, followed by the Heavenly sensation of something wet and cool gushing into her. It felt so good she cooed happily and bowed her back, which raised her ass, providing a better target.
“I’m glad you like it so far, Jenna,” she heard Mr. Hanson say. “I’ll bet you’re going to like the next thing I do even more.”
He would have won that bet, because the next thing that happened was a finger easing into the hole where nothing but her own finger had ever been inserted. She squealed in joy, and thrust her ass back to meet it, wanting to take it in even deeper, all the way until she felt his knuckles against the insides of her cheeks. When Brian Hanson moved the finger around to spread the lubricant, Jenna’s ass squirmed in pleasure. It was like nothing else she had ever felt, and she wanted more, and a lot of it, and as soon as she could get it.
“Oooo, Mr. Hanson, that was wonderful! I’ve never felt anything so wonderful.”
“That’s good, Jenna. I’m glad to hear that. As I said, some women prefer anal over other kinds of sex, and you might be one of those. You’re still tight, though, so I’m going to have to get my cock ready now.”
“Okay, but I hope you don’t take too long. I really want to feel that big dude in there.”
Brian was eager to get started too. He took no more time than he needed and, when he was done covering his cock with the Aqualube, gave further instructions to the young woman who was about to get the thrill of her life. “I’m ready. Reach back here and spread your ass cheeks. This will hurt at first, but just a little. If you feel a sharp pain, tell me and I’ll stop, because it’ll mean there’s something wrong.”
Avidly, Jenna did as she was told, even placing the tips of her fingers right against the edges of her rosebud and pulling them apart. Using the same thumb and fingers as he had used before, Brian pried the hole open slightly farther and, guiding his cock with the other hand, placed the tip against the small orifice. It took a firm but gentle push to squeeze the head into the tight place where they both wanted it.
As she had been warned, Jenna felt a slight burst of pain when the head of Mr. Hanson’s big, hard cock first wedged its way into her ass, but that was immediately overwhelmed by a great wave of pure pleasure that radiated out from the point of penetration. It felt so good to her that she moaned blissfully.
“Did that hurt?” Brian thought that his partner had expressed pleasure, rather than pain, but he wanted to be absolutely certain.
“Oh, no. It feels wonderful. It did hurt, but just a little at first. Now it feels really good.” Wanting much more of what felt so good, Jenna wiggled her hips invitingly at the man who would be supplying it.
“I’m glad, and it’ll feel even better the deeper I get my cock inside you.” Brian smiled at Jenna’s eagerness and, before making any further insertion, he used his finger to check all around the hole he would be stuffing, making sure there was no loose skin or other potential problem. He found none, and thrust another inch of his cock into her eager ass.
“Ahhhh,” she sighed, and bowed her back again canlı bahis siteleri while spreading her legs farther apart. Jenna was having a great time already, but her ass badly wanted more, so she presented a better target to the man who would be giving it to her.
Brian’s smile widened at her verbal and non-verbal expressions of delight, and plunged another inch of his hard shaft inside the hotty’s ass. She sighed again, and her back started writhing in front of him, silently begging for more. He wanted to give her all he had, and keep giving it to her over and over for a long time but, before doing that, he checked the penetration site again for any potential problems. There were none, and his cock was inside her deeply enough that he no longer needed to guide it. Brian removed his hands from where they had been spreading Jenna’s ass cheeks, wiped off the excess Aqualube, and placed them on her plump hips. Pulling against them for leverage, he drove most of the rest of his cock into the tight, well-lubricated hole.
The sexy blonde had never felt anything like it. Waves of pleasure, breakers even, surged out from where her ass was being crammed, and the waves became more powerful every time Brian’s cock went in more deeply. There was even a dividend that she could not have predicted. The fresh tampon in her pussy had soaked up all her bodily fluids and was filling that hole and starting to massage the sweet spots there. She had never felt that happen before, although she had worn hundreds of tampons during her life. Suddenly, she realized that the cock that was being stuffed into her ass was also squeezing her front pleasure hole, giving her a terrific double penetration, although Jenna was not yet familiar with the term.
It got even better when the last of Brian’s cock was imbedded. He stayed like that for almost a minute, reveling in the tightness of her ass, and her small, squirmy movements that turned into caresses of his shaft. It felt even better for Jenna, with more and greater breakers of joy crashing through her body, making her writhe and moan with bliss, and those movements made it even better. It was already some of the very best sex she had ever gotten, and the fucking had barely even started.
With his hands resting on Jenna’s soft hips, Brian slowly pulled his cock back, stopping when only the head remained inside her tight opening. He paused for a few seconds, before beginning to drive it back inside. When she felt the thick shaft surging into her, exquisite pleasure radiating out from along its path, Jenna fucked back to meet it. Brian ended up with the front of his pubic area pressed so tightly against the insides of Jenna’s ass cheeks that he could feel his hair being pressed flat against the soft skin. After leaving his cock inside her for most of a minute, letting it send intense pleasure throbbing through both of their bodies, he slowly pulled it almost all the way out again.
On the next stroke, Jenna once again thrust her ass back to meet the cock that was plunging into her, moaning happily as it burrowed its way, until the assistant dean’s body was once again pressed snugly against her cheeks. The thickness of his shaft spread open the entrance to her formerly virginal ass and expanded the attached channel and, this time, he left it inside her even longer before drawing it back out until only the head remained inside her.
Seconds later, when the big cock was pushing its way into her, Jenna’s ass met it again. At the same time, she reached around her cheeks, placed her fingers at the edges of the hole that was being stuffed so gloriously and spread them as far apart as she could. What she wanted was to hold her rosebud open enough to allow another fraction of an inch of the hard giver of pleasure to be driven through it and inside her, where it gave her so much more indescribable joy.
Over and over, Brian slowly plunged his cock into the blonde’s ass, which fucked back to meet him every time, while Jenna whimpered and sobbed from the excruciating pleasure. It was, by far, unlike anything she had ever felt before. Brian made a mental note to thank George again for his advice, because the Aqualube was working perfectly. The lubricant was fully liquefied by that time and, although his partner’s ass was as tight as it had been when they started, there was no friction at all. The only thing he could feel was the muscles inside her ass, rippling around the entire length of his shaft and massaging it as the hard cylinder plunged into her and when he drew it back out.
For a long time, they fucked, and Jenna’s movements became more and more erratic. Because she was supported by the couch, she couldn’t fall over, but her whole upper body writhed in front of and under Brian, and her hips swiveled, driving her knees into the floor. Those movements provided additional sensations, as Jenna’s ass massaged his cock in slightly different ways with every stroke.
Wanting to make the pleasure last as long as possible for both of them, Brian had been fucking very slowly, but he knew it couldn’t last much longer. His climax was building up, and he had been holding it back, knowing he would be cumming within a few minutes, and wanting Jenna to reach her orgasm first.
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